Sodium borohydride → (2R)-4-(5-Hydroxymethyl-3-trifluoromethyl-pyridin-2-yl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 912966ノート

反応式

HRID 912966 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([CH:24]=[O:25])=[CH:16][N:15]=2)[CH2:10][C@H:9]1[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]([F:23])([F:21])[F:22])=[CH:18][C:17]([CH2:24][OH:25])=[CH:16][N:15]=2)[CH2:10][C@H:9]1[CH3:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 11501642(2R)-4-(5-Formyl-3-trifluoromethyl-pyridin-2-yl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 11703510(2R)-4-(5-Hydroxymethyl-3-trifluoromethyl-pyridin-2-yl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of (2R)-4-(5-formyl-3-trifluoromethyl-pyridin-2-yl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester from step (e) above (4.48 g, 12 mmol) in methanol (30 mL) was added portionwise NaBH4 (542 mg, 14.4 mmol, Aldrich) with stirring at 0° C. The mixture was stirred at 0° C. for 30 min and the solvent was removed in vacuo. The residure was dissolved in EtOAc (60 mL) and washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with 50% EtOAc/hexane to give the title compound as a gum. MS (ESI, pos. ion) m/e: 376 (M+1).

後処理

  1. stirringThe mixture was stirred at 0° C. for 30 min
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residure was dissolved in EtOAc (60 mL)
  4. washwashed with water (20 mL) and brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by silica gel column chromatography
  9. washeluting with 50% EtOAc/hexane

出典と根拠

ORDレコード
ord-cbb09f95e9a2406e985e085ef771bb55
出典データセット
uspto-grants-2011_09
特許番号
US08026241B2

反応ノート

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